The Cross-Linking of Cotton Cellulose by Aliphatic Dicarboxylic Acids

Campbell, Hugh J.; Francis, Thomas

doi:10.1177/004051756503500310

Cited by 24 publications

(11 citation statements)

References 10 publications

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“…However, extensive research has attempted to develop nonformaldehyde crosslinking agents to replace N-methylol compounds that release formaldehyde during production and storage, which is suspected of being carcinogenic. Several polycarboxylic acids have been considered as durable press finishing agents for cotton fabrics [1][2]5]. The most effective is 1,2,3,4-butanetettacarboxylic acid (BTCA).…”

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confidence: 99%

Effect of Boric Acid and BTCA on Tensile Strength Loss of Finished Cotton Fabrics

Sricharussin

Ryo-Aree

Intasen

et al. 2004

Textile Research Journal

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Several polycarboxylic acids have been studied as durable press finishing agents for cotton fabrics. The most effective is 1,2,3,4-butanetetracarboxylic acid (BTCA). One of the drawbacks of this crosslinking is the severe loss of mechanical strength of the treated fabrics, which is responsible for the reduced durability of finished cotton garments. In this research, boric acid mixed with BTCA is considered as a remedy for this problem. Fourier transform infrared spectra, tensile tests, and crease recovery angle (CRA) measurements are used to investigate the effects of the treatment. The results reveal that if cotton fabrics are treated with the combination of BTCA and boric acid, they show high CRA values at a low curing temperature. In the presence of sodium hypophosphite as a catalyst, higher CRA values may be obtained, although at higher curing temperatures. Interestingly, adding boric acid to BTCA in the right proportions leads to almost complete retention of the mechanical strength originally present in the untreated cotton.Since the 1980s, the casual wear market has shown a steady increase in the demand for easy-care, creaseresistant cotton apparel. Formaldehyde-based N-methylol compounds, including dimethyloldihydroxylethyleneurea (DMDHEU) are the most widely used durable press finishing agents in the textile industry. However, extensive research has attempted to develop nonformaldehyde crosslinking agents to replace N-methylol compounds that release formaldehyde during production and storage, which is suspected of being carcinogenic. Several polycarboxylic acids have been considered as durable press finishing agents for cotton fabrics [ 1-2, 5]. The most effective is 1,2,3,4-butanetettacarboxylic acid (BTCA). It satisfies many desirable requirements such as durability to laundering and durable press performance [6]. Cellulose esterification by a polycarboxylic acid proceeds in two steps: first a cyclic anhydride intermediate is formed, and this intermediate then reacts with cellulose to form an ester [7]. Infrared spectroscopic (IR) data also demonstrate that cyclic anhydrides are very reactive and able to esterify cellulose without a catalyst present [8].One of the drawbacks of crosslinked durable-press cotton fabrics is the loss of mechanical strength. Severe tensile strength loss diminishes the durability of finished cotton garments. The factors involved in strength loss of cottons treated with BTCA include acid catalyzed degradation of cellulose molecules and their crosslinking [3]. However, fabric strength loss due to crosslinking is reversible, as shown by removing the crosslinking by hydrolysis under alkaline conditions. The common catalysts for polycarboxylic acids are phosphorous-containing compounds, although their use has disadvantages such as high cost and raises some environmental concerns. Other catalysts have been proposed ; among these is boric acid, which was added to maintain whiteness in the treated fabrics [4]. With this treatment, durable press properties were similar to those obtaine...

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confidence: 99%

Effect of Boric Acid and BTCA on Tensile Strength Loss of Finished Cotton Fabrics

Sricharussin

Ryo-Aree

Intasen

et al. 2004

Textile Research Journal

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“…The adipate group was selected versus other possible x-carboxy cellulose esters since it is the shortest chain possible that would provide an unfavorable transition state (7-membered ring in this case) for autocatalysis of the ester linkage, promoting good hydrolytic stability. Synthesis of pure, well-characterized cellulose adipates had to our knowledge been unknown in the literature, prior to our recent work (Kar et al 2011); the only pertinent prior reports dealt with reaction of cellulose fibers and surfaces with adipic acid to cross-link and modify textile properties (Campbell and Francis 1965;Rowland and Brannan 1968). Kar et al reported that a direct approach to the synthesis of cellulose adipate esters, by reaction of cellulose or cellulose esters in solution with adipic anhydride, was plagued by problems of rapid gelation.…”

Section: Introductionmentioning

confidence: 99%

Direct synthesis of cellulose adipate derivatives using adipic anhydride

2012

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The poor aqueous solubility of many drugs can be overcome by formulation as amorphous solid dispersions (ASD) in cellulosic-based polymer matrices. Cellulose esters containing adipates and other ester groups have shown great promise as new ASD polymers. Previous attempts to synthesize these cellulose adipate esters by direct reaction of cellulose derivatives with adipic anhydride failed due to crosslinking and gelation, caused by formation of poly (adipic anhydride) and subsequent reaction of the poly (anhydride) with cellulosic hydroxyls. In order to develop direct, efficient syntheses of these pH-sensitive cellulose adipate derivatives, we have developed new synthetic procedures that cleanly afford soluble ester products by direct condensation with adipic anhydride, that show no evidence of crosslinking. A series of cellulose ester adipates has been synthesized by this direct route, containing substantial adipate DS (up to 0.53). This new method requires no complex solvents or protective groups, and is an effective and versatile route to these useful materials.

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“…[1][2][3] However, the performance of the crosslinked cotton fabrics was not satisfactory because the catalysts used were not efficient enough to ensure effective crosslinking of cellulose. Since the late 1980s, extensive efforts have been made to use polycarboxylic acids as durable press finishing agents for cotton to replace the formaldehyde-based dimethyloldihydroxylethyleneurea (DMDHEU) due to the increasing concern with the toxicity of formaldehyde.…”

Section: Introductionmentioning

confidence: 99%

Crosslinking cotton with poly(itaconic acid) and in situ polymerization of itaconic acid: Fabric mechanical strength retention

Yang

Lickfield

2003

J of Applied Polymer Sci

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Polycarboxylic acids have been used as nonformaldehyde durable press finishing agents for cotton fabrics. Previously, we found that itaconic acid (IA) polymerized in situ on cotton fabric and also in an aqueous solution in the presence of a K 2 S 2 O 8 /NaH 2 PO 2 initiation system. Both poly(itaconic acid) (PIA) and the polymer formed by in situ polymerization of IA are able to crosslink cotton cellulose, thus imparting wrinkle resistance to cotton. In this research, we compared the performance of the cotton fabric crosslinked by PIA and that crosslinked by in situ polymerization of IA. The fabric treated with PIA and that treated with IA had similar wrinkle recovery angles. The cotton fabric treated with IA, however, lost more tensile strength than that treated with PIA due to cellulose degradation. We determined the magnitude of the fabric tensile strength loss attributed to crosslinking by separating the tensile strength loss due to cellulose degradation from the total tensile strength loss, and found that the tensile strength loss caused by crosslinking for the fabric treated with PIA was significantly higher than that for the fabric treated with IA. This can probably be attributed to more concentrated crosslinkages formed on the near surface of the PIA-treated cotton fabric. PIA had poorer penetration into the amorphous cellulose region in fiber interior due to its much larger molecular size, thus increasing its concentration on the fabric's near surface. The data also suggest that more concentrated crosslinkages on the fabric surface reduced fabric abrasion resistance.

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The Cross-Linking of Cotton Cellulose by Aliphatic Dicarboxylic Acids

Cited by 24 publications

References 10 publications

Effect of Boric Acid and BTCA on Tensile Strength Loss of Finished Cotton Fabrics

Effect of Boric Acid and BTCA on Tensile Strength Loss of Finished Cotton Fabrics

Direct synthesis of cellulose adipate derivatives using adipic anhydride

Crosslinking cotton with poly(itaconic acid) and in situ polymerization of itaconic acid: Fabric mechanical strength retention

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